[Form 4] Wintrust Financial Corp Insider Trading Activity

Rhea-AI Filing Summary

Morgan Stanley Finance LLC (ticker: MS) has filed Amendment No. 1 to Pricing Supplement No. 8,667 for a $440,000 follow-on issuance of Dual Directional Buffered PLUS notes (CUSIP 61778KD61) that will be consolidated with the original $310,000 tranche, bringing the total outstanding to $750,000. The five-year structured notes, due 28 Jun 2030, are unsecured and fully guaranteed by Morgan Stanley.

Key economic terms

• Issue price: $1,000; minimum denomination $1,000.
• Estimated value on pricing date: $943.80 (reflecting structuring & hedging costs).
• Underlying indices: DJIA (INDU 42,982.43), Nasdaq-100 (NDX 22,237.74) and Russell 2000 (RTY 2,136.185).
• Leverage factor: 140% on any positive performance of the worst-performing index.
• Absolute return participation: 100% of any decline up to 20%, effectively capping gain from this feature at 20%.
• Buffer: 20% downside protection; losses begin once the worst performing index falls below 80% of its initial level.
• Minimum maturity payment: 20% of principal.
• No periodic coupons; payment occurs only at maturity.

Cash-flow profile

• Upside scenario: final level > initial level → principal plus 1.4× index appreciation.
• Moderate downside: final level between 80% and 100% of initial → principal plus up to 20% gain.
• Severe downside: final level < 80% of initial → 1:1 loss beyond buffer, floor at 20% of principal.

Placement economics: Investors pay a 3.5% sales commission ($35 per note); net proceeds to Morgan Stanley are $965 per note. The notes will not be listed, and secondary liquidity depends solely on MS & Co., which may discontinue market making at any time.

Risk highlights

• Principal at risk; no interim interest.
• Performance driven solely by the worst performing index, eliminating diversification benefits.
• Credit exposure to Morgan Stanley; notes rank pari passu with other unsecured obligations.
• Estimated value below issue price indicates negative carry at inception.
• Tax treatment uncertain; counsel views notes as prepaid financial contracts, but IRS may disagree.

Strategic context: At $0.75 million aggregate size, the issuance is immaterial to Morgan Stanley’s capital structure but offers the bank low-cost funding while transferring market risk to investors.

Positive

• 140% upside leverage enhances returns when all indices appreciate.
• 20% downside buffer and minimum 20% maturity payout provide partial principal protection.
• Absolute return participation allows positive return in a flat-to-moderately down market.
• Fully guaranteed by Morgan Stanley, a large investment-grade issuer.

Negative

• Principal at risk beyond 20% buffer; losses can reach 80% of invested amount.
• Performance tied to worst-performing index, nullifying diversification benefits.
• Estimated value ($943.80) below issue price implies negative carry from day one.
• No periodic coupons; investors forgo income for five years.
• Unlisted, dealer-driven secondary market may result in illiquidity and wide spreads.
• Exposure to Morgan Stanley credit risk; notes are unsecured obligations.

Insights

Structured Products Analyst

TL;DR – High-risk, niche note offers 140% upside leverage with 20% buffer and minimum 20% payout, but principal is unsecured and illiquid.

The amended 424B2 adds $440k to an existing tranche, keeping economic terms intact. Investors gain an attractive 1.4× upside and a limited absolute-return feature, but face three headwinds: (1) real economic value starts at $943.80—3 points below par; (2) downside kicks in once any one index breaches an 20% drawdown, nullifying diversification; and (3) secondary liquidity is dealer-driven, exposing holders to wide bid–ask spreads. From Morgan Stanley’s standpoint, the deal provides cheap fixed-rate funding and fee income. Impact on MS equity is negligible, so I rate it 0 (Neutral).

Risk Analyst

TL;DR – Note concentrates risk on worst index; buffer & floor mitigate only first 20% loss—investors could lose up to 80% of principal.

Credit risk is paramount: as an MSFL obligation, recovery hinges solely on Morgan Stanley’s guarantee. Market risk is amplified by linking payout to the lowest-performing of three volatile benchmarks, including small-cap Russell 2000. While the 20% buffer appears protective, historical data show multiple 30%+ one-year drawdowns in all three indices. Liquidity risk is also material; the $750k total size limits aftermarket depth. Given the potential for substantial capital loss relative to capped upside, I assign a -1 (Negative) impact rating for prospective note investors (though not for MS shareholders).

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Smith Gregory A

(Last) (First) (Middle)

9700 WEST HIGGINS ROAD, 8TH FLOOR

(Street)

ROSEMONT IL 60018

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
WINTRUST FINANCIAL CORP [ WTFC ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

X	Director		10% Owner
	Officer (give title below)		Other (specify below)

3. Date of Earliest Transaction (Month/Day/Year)
06/30/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Common Stock	06/30/2025		A		402(1)	A	$112.46	2,381	D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares

Explanation of Responses:

1. Shares earned for the second quarter of 2025 for services as a Director of the Company in accordance with the Director's Deferred Fee and Stock Plan approved by the Shareholders.

Remarks:

	/s/Kathleen M. Boege, Attorney-in-fact	07/02/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

What indices underlie Morgan Stanley’s Dual Directional Buffered PLUS (MS)?

The note references the Dow Jones Industrial Average, Nasdaq-100, and Russell 2000; payout depends on the worst performer.

How much upside can investors earn on the MS Buffered PLUS notes?

If the worst index rises, investors receive 140% of that gain with no cap; if it falls ≤20%, gains are capped at 20%.

What is the downside protection and floor for the MS 424B2 notes?

There is a 20% buffer; beyond that investors lose 1% per 1% decline, but payment will not fall below 20% of principal.

Why is the estimated value ($943.80) below the $1,000 issue price?

The gap reflects structuring, hedging, distribution costs and the issuer’s lower internal funding rate.

Are the notes liquid and exchange-traded?

No; they are unlisted. Liquidity depends solely on MS & Co. making a market, which it may discontinue.

What are the key tax considerations for non-U.S. holders?

Counsel believes Section 871(m) should not apply before 2027, but the IRS could disagree; investors should seek tax advice.